Your Italy. Your Way.
Where Renaissance light warms ancient stones and golden coasts.
Italy:
Where Every Stone Tells a Story
Italy isn’t just a destination — it’s a way of living beautifully. From Rome’s timeless forums to Venice’s shimmering canals, from Tuscan vineyards to Amalfi’s cliffside villages, every region tells a story shaped by art, flavor, and light. Here, mornings linger over cappuccinos, afternoons wander through marble halls and olive groves, and evenings unfold slowly at tables made for conversation.
At Latitude & Leisure, we design Italy around your rhythm: iconic masterpieces balanced with quiet courtyards, private tastings between vineyard rows, and boat days where the only plan is the horizon. Our insider access and thoughtful pacing turn a dream itinerary into a seamless flow — less about checking boxes and more about feeling the dolce vita.
Plan Your Dream Italy Journey
Not sure where to start? Begin with the Italy Bucket List — a curated guide designed to spark inspiration and help you organize the must-do experiences. Then, explore a Sample Itinerary to see how la dolce vita comes to life — from timeless piazzas to sun-drenched coastlines.
Regions That Shape the Journey
Every region in Italy holds its own story — these are the places that shape the journey.
Eternal City, Timeless Charm
Rome moves to an ancient heartbeat. Stand beneath the Colosseum’s arches as sunlight spills across travertine; trace marble footsteps through the Forum where empires rose and fell; then slip into a neighborhood trattoria where the day’s stories are served with cacio e pepe and a glass of Lazio red. In Rome, history isn’t behind museum glass — it’s the stage you walk across.
With the right timing, the city reveals softer notes: early-morning Vatican galleries before doors open, a private guide in the Borghese sharing Caravaggio’s secrets, twilight on a rooftop terrace as church domes glow to life. Between espresso bars and elegant piazzas, Rome becomes more than eternal — it becomes effortless.
Highlights: Colosseum & Forum · Vatican Museums & Sistine Chapel (early access) · Trastevere trattorias · Borghese Gallery · Rooftop aperitivos · Hidden fountains & courtyards
Renaissance Soul & Rolling Hills
Tuscany is a poem written in soft, golden light. In Florence, Renaissance masters still speak from stone and canvas — Brunelleschi’s dome, Botticelli’s spring, Michelangelo’s marble. Step beyond the city and the hills open: cypress-lined lanes, farmhouse kitchens, and vineyards where time slows to the pace of a long lunch.
Your days stretch beautifully here — a private Uffizi tour before the crowds, then a drive to a family estate for an olive-oil tasting and a table set under pergola shade. Sunset catches the terracotta rooftops, and the evening lingers over bistecca and Brunello. Tuscany invites you to savor — and stay awhile.
Highlights: Uffizi & Accademia (priority entry) · Chianti & Montalcino wineries · Siena & San Gimignano hill towns · Farm-to-table lunches · Truffle foraging (seasonal) · Artisan studios & leather workshops
Floating City of Dreams
Venice is a watercolor come to life — reflections of palazzi on still canals, bridges that turn corners into surprises, and a hush that settles when you leave the main thoroughfares. Arrive by water taxi and the city feels like a secret shared only with you. Wander by day through hidden campos and light-filled galleries; glide at dusk when the lagoon blushes and the city exhales.
With insider guidance, you’ll meet Venice beyond the postcard: a private visit to a quiet chapel where Tintorettos glow; cicchetti tastings in bàcari known by locals; a boat to Murano at opening bell to watch glass breathe into shape. Venice rewards unhurried curiosity — and a willingness to get a little lost.
Highlights: St. Mark’s Basilica & Doge’s Palace (after-hours) · Grand Canal by private boat · Cicchetti crawl · Murano glass & Burano lace · Hidden churches & artisan ateliers
Cliffs, Color & Coastline
The Amalfi Coast is a ribbon of color stitched into cliffs — lemon groves, pastel villages, and the deep, glittering Tyrrhenian. Days begin on a terrace where bougainvillea frames the sea; they carry on by convertible or private boat, ducking into coves and lunching where the catch lands minutes before it’s grilled. Evenings are for soft linen, candlelight, and the slow page-turn of a perfect meal.
Beyond the views, there’s rhythm: a hike along the Path of the Gods with a guide who grew up on these slopes; a limoncello tasting in a family garden; Ravello’s music floating above sea and sky. With the right plan, traffic fades and the coast opens — effortless, elegant, unforgettable.
Highlights: Private boat day (Capri & grottoes) · Positano & Ravello · Path of the Gods hike · Lemon grove tastings · Cliffside dining · Coastal convertible drives
Alpine Elegance Meets Tranquility
Como is where mountains meet mirrored water and villas keep stories behind shuttered windows. Mornings glide by on wooden launches past camellia gardens and stone stairways; afternoons find you on grand terraces, bells drifting across the lake as light moves up the peaks. Each village — Bellagio, Varenna, Tremezzo — holds its own charm.
Stay lakeside and live slowly: garden picnics, a chef’s tasting with lake fish and local nebbiolo, a funicular ride for blue-hour views. Add day trips into the Alps or to the Franciacorta wine region, and the elegance deepens. Como’s beauty is quiet — that’s its luxury.
Highlights: Private wooden boat tour · Villa Carlotta & Villa Balbianello gardens · Bellagio & Varenna strolls · Lakeside aperitivi · Alpine day trips · Franciacorta sparkling wineries
Sun-Warmed Mosaic
Sicily is Italy’s sun-warmed mosaic — Greek temples, Baroque towns, Arab gardens, volcanic soil, and a coastline that shifts from dramatic to dreamy in a single drive. Stand under Doric columns in Agrigento, wander honey-colored streets in Noto, and taste foods shaped by centuries of arrivals: pistachio, citrus, saffron, sea.
With thoughtful pacing, Sicily becomes a revelation: a sunrise hike on Mount Etna followed by a rustic winery lunch; a fisherman’s boat to hidden coves near Ortigia; a private guide who unlocks Palermo’s markets and Norman chapels. This is Italy at its most layered — generous, soulful, and gloriously alive.
Highlights: Valley of the Temples · Mount Etna & boutique wineries · Ortigia & Syracuse · Baroque towns (Noto, Ragusa, Modica) · Palermo markets & mosaics · Seaside reserves & coves
Signature Ways to Explore — Expertly Crafted Journeys
There’s no single way to experience Italy — only the one that’s right for you. We pair iconic moments with insider access, thoughtful timing, and a touch of effortless luxury to make each region unforgettable.
Cultural Heritage Trail
Ancient Cities & Masterpieces
Private historians bring Rome, Florence, and Venice to life with exclusive access and stories that stay with you.
Coastal Luxury Escape
Amalfi, Capri & Riviera Glow
Seaside villas, sunset sailings, and cliffside dining define this indulgent Mediterranean rhythm.
Countryside Odyssey
Vineyards, Villas & Slow Living
Tuscany, Umbria, and the Northern Lakes — olive groves, farmhouse kitchens, and tastings among the vines.
Grand Italian Journey
Rome • Tuscany • Venice • Amalfi
A seamless multi-region flow crafted for travelers who want the sweep of Italy — without the rush.
Seasonal Feature: Harvest Season — Late September to November brings grape harvests, truffle hunts, and golden countryside light. Secure guides and tastings well in advance.
Best Time to Journey
Italy’s beauty shifts with the seasons, making when you go just as meaningful as where you go.
Peak Season
May–September
Warm days, long evenings, and lively piazzas. Ideal for coastal escapes, lake stays, and open-air culture.
Shoulder Season
April & October
Mild weather and softer crowds — perfect for city breaks, wine country, and long lunches.
Winter Highlights
November–March
Quieter museums, festive markets, Alpine getaways, and cozy culinary journeys.
Festive Season
December
Nativity art, sparkling streets, and regional feasts — best booked well ahead.
Travel Tip: Iconic experiences — Vatican early access, Amalfi boat days, villa stays, and top museum entries — book out quickly. Reserve early for the best timing and views.
Insider Planning Tips
A little thoughtful planning goes a long way in Italy. With its varied regions and rich cultural calendar, the magic is in the pace — and in leaving room to savor.
- Pack for versatility — Italy’s climate varies by region and season. Lightweight layers, a chic day-to-night outfit, and comfortable shoes are key. A light jacket or wrap will serve you well on cool evenings or when visiting hilltop villages and vineyards.
- Time your experiences — Early mornings and evenings bring softer light, fewer crowds, and a more romantic atmosphere at Italy’s most famous landmarks. Plan mid-day breaks at cafés, piazzas, or your hotel to slow down and savor la dolce vita.
- Embrace regional flavor — Italy isn’t just one cuisine—it’s a tapestry of local traditions. Indulge in cicchetti in Venice, handmade pasta in Rome, aperitivo in Florence, and seafood on the Amalfi Coast. Food is part of the journey; let your palate lead the way.
- Move smartly — Trains offer a scenic and efficient way to explore between major cities, while private drivers or transfers make countryside and coastal travel effortless. Pack light to keep your transitions smooth.
- Mind the midday pace — Many shops, wineries, and small villages pause during the afternoon, especially in summer. Use this time for a leisurely lunch, poolside relaxation, or a stroll through shaded streets.
- Celebrate the seasons — Travel in late spring or early fall for pleasant weather, vibrant markets, and harvest festivals. Summer brings lively energy and long evenings, while winter offers quieter cities and festive charm.
Your Italy Journey, Answered
Your questions are where the journey begins. Here’s what travelers ask most — and how Latitude & Leisure turns answers into effortless escapes.
Can I travel Italy without speaking Italian?
Yes — Italy is wonderfully welcoming to travelers. Most hotels, major train stations, and tourism sites have English-speaking staff or signage, and we provide tools and guidance to make getting around easy.
For deeper, more local experiences — like vineyard tours or countryside stays — we can arrange private guides, hosts, or translators so language never becomes a barrier to connection.
What’s the best time to visit Italy?
Italy is beautiful year-round, and each season has its own rhythm:
- Spring (April–May): Warm, blooming landscapes, perfect for cities and countryside.
- Summer (June–September): Vibrant festivals, coastlines, and long sunny days.
- Autumn (October–November): Wine harvest, truffle season, golden light.
- Winter (December–March): Quiet cities, festive markets, Alpine escapes.
We’ll match your travel style to the season — whether you dream of vineyard picnics, coastal boat days, or cozy winter villas.
How many regions should I visit on my first trip?
For most travelers, 2–3 regions offers the best balance of depth and flow. A classic route might be Rome → Florence/Tuscany → Amalfi Coast, blending history, culture, and natural beauty.
Longer trips can weave in Venice, the Northern Lakes, or Sicily. Our itineraries are designed to feel seamless — never rushed.
Do I need to rent a car in Italy?
Not always. Italy’s high-speed trains make traveling between cities (Rome, Florence, Venice, Milan) fast and scenic. For countryside regions like Tuscany or the Amalfi Coast, a private driver or short rental can offer extra flexibility.
We’ll help you choose the best option for your route and comfort level.
Is Italy crowded in summer?
Yes — peak season (June through early September) is lively, especially in major cities and coastal areas. To make it feel effortless, we time activities around crowds: early entry to landmarks, private tours, and off-hour excursions. Shoulder season is perfect for travelers seeking fewer tourists and mild weather.
How far in advance should I plan my trip?
For popular experiences like Vatican early access, Amalfi boat days, and villa stays, we recommend booking 6–9 months in advance. Shoulder and winter trips can often be planned closer, but early planning always opens more options.
What’s the best way to get around Italy?
Trains are excellent for major cities. High-speed lines connect Rome, Florence, Venice, and Milan in just a few hours. For countryside or coast, we arrange private transfers, drivers, or short car rentals.
We build your itinerary to minimize transfers and maximize ease.
Should I visit Sicily or the Northern Lakes on my first trip?
It depends on your style. Sicily is soulful, warm, and layered with history — ideal for those who love culture and food. Lake Como and the North offer elegance, Alpine views, and quiet luxury. Either can be seamlessly added to a classic Italy route if time allows.
Do I need to tip in Italy?
Tipping isn’t mandatory, but rounding up or leaving 5–10% at restaurants is appreciated for good service. For private guides and drivers, small gratuities are customary but never required.
If I’m traveling for a specific sport or passion (such as scuba diving, golfing, or skiing), where should I go?
Italy is an extraordinary destination for both culture seekers and active travelers.
- Scuba Diving & Snorkeling: The Amalfi Coast, Sardinia, and Sicily offer clear waters, underwater caves, and marine reserves.
- Golfing: Tuscany, Lake Como, and Rome are home to some of Europe’s most scenic courses.
- Skiing & Winter Sports: The Dolomites in northern Italy are world-class for skiing, snowboarding, and alpine experiences.
- Cycling & Hiking: Tuscany’s rolling hills, Cinque Terre’s coastal trails, and Lake Garda are ideal for active explorations.
What are the key festivals or holidays in Italy?
Carnivale di Venezia (February) – Venice transforms into a citywide masquerade. Expect large crowds, elevated hotel rates, and magical evening parades. Book well in advance.
Easter (Pasqua) – Churches hold major processions; many shops and some attractions close on Easter Sunday and Monday. Historic towns come alive with tradition.
Festa della Repubblica (June 2) – Parades and celebrations in major cities; public offices close, but tourist attractions typically remain open.
Palio di Siena (July & August) – A unique medieval horse race; Siena is crowded and festive. Hotels sell out early.
Ferragosto (August 15) – Italians vacation en masse. Some smaller businesses close, especially in cities, while coastal areas are very busy.
Christmas Markets (December) – A festive season with illuminated squares, markets, and winter activities.
What should I pack for Italy?
Pack breathable layers, comfortable walking shoes (for cobblestones), and one polished outfit for evenings out. A light jacket or scarf works well for spring and autumn. Keep luggage flexible — Italy rewards those who travel light.
Can Italy be combined with another country?
Absolutely. Italy pairs beautifully with France, Switzerland, Greece, or even Croatia. Many routes can be arranged via short flights or scenic trains. We’ll help design a journey that flows without travel-day stress.
What’s something special Latitude & Leisure can arrange?
Private access to the Vatican Museums at dawn, a truffle hunt with a local family in Tuscany, a private boat along the Amalfi Coast, or a chef’s tasting in a hidden vineyard. These insider touches are what turn a great trip into a once-in-a-lifetime journey.
Discover Italy, Curated Your Way
Discover the art of travel, Italian style—passionate, timeless, and delightfully unhurried.
From Tuscan vineyards to Venetian canals, our curated journeys blend culture and cuisine, romance and rhythm. Every experience celebrates la dolce vita—crafted for travelers who savor every moment of the journey.
La Dolce Journey
Stroll ancient streets, sip local wines, and explore hilltop towns steeped in art, history, and heart.
Coastal Reverie
Cruise past Capri, the Amalfi Coast, or Sicily—seaside elegance with a taste of Mediterranean sun.
Culinary & Culture
Savor Italy through its passions—regional flavors, master craftsmanship, and the joy of connection.
